In recent years, higher education institutions have made efforts to attract people who are either in the labor market or unemployed to the educational system. Accordingly, the participation of nontraditional students in postsecondary education has been increasing over the years in Portugal, including working students and working student parents. This growing phenomenon has received relatively little empirical attention since few country-level studies have been conducted targeting the combination of school with other life roles with a nontraditional student population enrolled in postsecondary education. The current study investigates the combination of school with other life roles for nontraditional Portuguese students enrolled in postsecondary education. Participants were 73 working student parents (enrolled in full-time undergraduate programs). Structural equation modeling (SEM) analysis was used to test the model. The coexistence of school-family conflict and school-family enrichment was found. Gender differences on the antecedent variables of school-family conflict and enrichment were also found, emphasizing the advantage in examining conflict and enrichment experiences simultaneously and by gender when investigating school and family relations. Implications of the findings and suggestions for future research are discussed.